CN111909172B - Oxygen-containing multi-heterocyclic compound and application thereof - Google Patents

Oxygen-containing multi-heterocyclic compound and application thereof Download PDF

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CN111909172B
CN111909172B CN202010755988.8A CN202010755988A CN111909172B CN 111909172 B CN111909172 B CN 111909172B CN 202010755988 A CN202010755988 A CN 202010755988A CN 111909172 B CN111909172 B CN 111909172B
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CN111909172A (en
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李继响
梁现丽
段陆萌
杭德余
曹占广
班全志
陈婷
赵风月
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Beijing Yanhua Jilian Optoelectronic Technology Co ltd
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Abstract

The invention relates to a novel oxygen-containing multi-heterocyclic compound which has a structure shown as a general formula (I), and R of the structure 1 ～R 12 In the formula (I), at least one group is a substituted or unsubstituted aromatic group containing a five-membered heterocycle, and the aromatic group containing the five-membered heterocycle is connected with a mother nucleus shown in a general formula (I) through a C atom. The novel OLED material provided by the invention takes a compound with a multi-heterocyclic structure as a matrix, and an electron-donating group is introduced into the matrix structure, so that the novel OLED material which has a high triplet state energy level, a good carrier mobility, a high thermal stability and a high film forming stability and can be matched with the energy level of an adjacent layer is obtained. The material can be applied to the field of organic electroluminescence, can be used as a green light main body material, and can effectively improve the photoelectric property of a device.

Description

Oxygen-containing multi-heterocyclic compound and application thereof
Technical Field
The invention belongs to the technical field of organic electroluminescence display, and particularly relates to a novel oxygen-containing multi-heterocyclic compound and application thereof in an organic electroluminescence (OLED) device.
Background
The application of the organic electroluminescent (OLED) material in the fields of information display materials, organic optoelectronic materials and the like has great research value and good application prospect. With the development of multimedia information technology, the requirements for the performance of flat panel display devices are higher and higher. The main display technologies at present are plasma display devices, field emission display devices, and organic electroluminescent display devices (OLEDs). The OLED has a series of advantages of self luminescence, low-voltage direct current driving, full curing, wide viewing angle, rich colors and the like, and compared with a liquid crystal display device, the OLED does not need a backlight source, has wider viewing angle and low power consumption, has the response speed 1000 times that of the liquid crystal display device, and has wider application prospect.
Since OLEDs were first reported, many scholars have been working on how to improve device efficiency and stability. Forrest and Thompson research groups find that the transition metal complex can be applied to Ph OLEDs (phosphorescent OLEDs), the phosphorescent material has strong spin-orbit coupling effect, and singlet excitons and triplet excitons can be simultaneously utilized, so that the quantum efficiency in the phosphorescent electroluminescent device theoretically reaches 100%. However, phosphorescent materials have longer excited state lifetimes, and are prone to triplet-triplet extinction and triplet-polaron- extinction when triplet exciton concentrations are higher. Phosphorescent materials are often incorporated as guest into host materials to reduce self-concentration quenching processes. Therefore, it is also an important matter to select a suitable host material in Phosphorescent organic electroluminescent devices (Ph OLEDs). Essential characteristics of the host material: (1) possess a higher triplet energy level; (2) The carrier mobility is better and can be matched with the energy level of the adjacent layer; (3) has high thermal stability and film forming stability.
At present, OLED display and illumination are widely commercialized and applied, the requirements of a client terminal on the photoelectricity and service life of an OLED screen body are continuously improved, in order to meet the requirements, in addition to the refinement and refinement on the OLED panel manufacturing process, the development of OLED materials capable of meeting higher device indexes is very important. Therefore, a stable and efficient main body material is developed, so that the driving voltage is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the method has important practical application value.
Disclosure of Invention
The invention aims to provide a novel OLED host material with low driving voltage and high luminous efficiency for a device, and application of the organic material in an OLED device.
Specifically, the first object of the present invention is to provide a novel oxygen-containing polyheterocyclic compound having a structure represented by the general formula (I):
Figure BDA0002611575710000011
in the general formula (I), R 1 ～R 12 At least one group is a substituted or unsubstituted aromatic group containing a five-membered heterocycle, and is connected with a mother nucleus shown in a general formula (I) through a C atom; the remaining groups each independently represent a hydrogen atom, a halogen, a linear or branched alkyl group, a cycloalkyl group, an amino group, an alkylamino group, a substituted or unsubstituted aromatic group containing a benzene ring and/or an aromatic heterocyclic ring.
As a preferred embodiment of the present invention, the substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring contains at least one five-membered heterocyclic ring, preferably one, two or three five-membered heterocyclic rings. The five-membered heterocyclic ring contains at least one heteroatom, preferably one, two or three heteroatoms. The heteroatom is optionally selected from the group consisting of N atom, S atom and O atom; when the substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring contains a plurality of hetero atoms, the respective hetero atoms may be the same as each other, may be partially the same as each other, or may be different from each other.
As a preferred embodiment of the present invention, the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from: substituted or unsubstituted carbazolyl, substituted or unsubstituted indoloindolyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl.
In a preferred embodiment of the present invention, in the substituted aromatic group containing a five-membered heterocycle, the substituent may be optionally selected from: phenyl, naphthyl, biphenyl, benzo, naphtho, phenanthro, indolo (e.g., N-benzaindolo), benzothieno, benzofuro. The number of substituents is selected from an integer of 1 to 5, preferably 1 to 3.
As a preferred embodiment of the present invention, the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from:
Figure BDA0002611575710000021
Figure BDA0002611575710000031
Figure BDA0002611575710000041
preferably, the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from:
Figure BDA0002611575710000042
Figure BDA0002611575710000051
further preferably, the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from the group consisting of:
Figure BDA0002611575710000052
in each of the above-mentioned substituent groups, "- - -" represents a substitution position.
As a preferred embodiment of the present invention, R is 1 ～R 12 Any one of the groups is a substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring.
As a preferred embodiment of the present invention, R is 1 ～R 12 Wherein any two groups are substituted or unsubstituted aromatic groups containing five-membered heterocyclic rings; the two groups may be the same or different.
As a preferred embodiment of the present invention, R is 1 ～R 4 Any two of the groups are substituted or unsubstituted aromatic groups containing five-membered heterocyclic rings; or, said R 5 ～R 8 Any two of the groups are substituted or unsubstituted aromatic groups containing five-membered heterocyclic rings; or, said R 9 ～R 12 Any two of the groups are substituted or unsubstituted aromatic groups containing five-membered heterocyclic rings; or, said R 1 ～R 4 Any one of the groups and R 5 ～R 8 Any one of the groups is a substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring; or, said R 1 ～R 4 Any one of the groups and R 9 ～R 12 Any one of the groups is a substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring; or, said R 5 ～R 8 Any one of the groups and R 9 ～R 12 Any one of the groups is a substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring.
As a preferred embodiment of the present invention, R is 1 ～R 12 In the above formula, any three groups are substituted or unsubstituted aromatic groups containing a five-membered heterocycle, and the three groups may be the same, any two of the groups may be the same, and the other group may be different, or each group may be different.
As a preferred embodiment of the present invention, R is 1 ～R 4 Any two of them and R 5 ～R 8 Any one of the groups is a substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring; or, said R 1 ～R 4 Any two of them and R 9 ～R 12 Any one of the groups is a substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring; or, said R 5 ～R 8 Any two of them and R 1 ～R 4 Any one of the groups is a substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring; or, said R 5 ～R 8 Any two of them and R 9 ～R 12 Any one of the groups is a substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring; or, said R 9 ～R 12 Any two of them and R 1 ～R 4 Any one of the groups is a substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring; or, said R 9 ～R 12 Any two of (1) and R 5 ～R 8 Any one of the groups is a substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring; or, said R 1 ～R 4 Any one of the groups R 5 ～R 8 Any one of the groups and R 9 ～R 12 Any one of the groups is a substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring.
As a preferred embodiment of the present invention, R is 1 ～R 12 Wherein the remaining groups are hydrogen atoms except any one, two or more of the aromatic groups which are substituted or unsubstituted and contain a five-membered heterocyclic ring.
As a preferable scheme of the invention, the novel oxygen-containing multi-heterocyclic compound is selected from structures shown in formulas I-1 to I-190:
Figure BDA0002611575710000061
Figure BDA0002611575710000071
Figure BDA0002611575710000081
Figure BDA0002611575710000091
Figure BDA0002611575710000101
Figure BDA0002611575710000111
Figure BDA0002611575710000121
Figure BDA0002611575710000131
Figure BDA0002611575710000141
the organic compound takes a multi-heterocyclic ring structure as a matrix, the matrix structure has good thermal stability and appropriate HOMO and LUMO energy levels and Eg, and a group with electron donating capability is introduced into an active position in the matrix structure, namely a five-membered heterocyclic ring structure such as carbazole, furan, thiophene and the like with electron donating capability is introduced into the structure, so that the OLED material with a novel structure is obtained. The organic light emitting diode is applied to an OLED device and used as a green light main body material, the photoelectric property of the device can be effectively improved, and the device can be applied to the field of display or illumination.
The second purpose of the invention is to provide the application of the oxygen-containing multi-heterocyclic compound in preparing organic electroluminescent devices. The oxygen-containing multi-heterocyclic compound can be used as a green host material of an EML (electron emission layer) in an organic electroluminescent device.
The third object of the present invention is to provide an organic electroluminescent device comprising an electroluminescent layer, wherein the host material of the electroluminescent layer contains the oxygen-containing heterocyclic compound of the present invention. The thickness of the electroluminescent layer may be 10 to 50nm, preferably 20 to 40nm.
Specifically, the invention provides an organic electroluminescent device, which sequentially comprises a transparent substrate, an anode layer, a hole transport layer, an electroluminescent layer, an electron transport layer, an electron injection layer and a cathode layer from bottom to top, wherein a light-emitting main body material of the electroluminescent layer comprises the oxygen-containing multi-heterocyclic ring compound shown in the general formula (I) provided by the invention.
It is a fourth object of the present invention to provide a display apparatus comprising the organic electroluminescent device.
A fifth object of the present invention is to provide a lighting device including the organic electroluminescent device.
In conclusion, the novel oxygen-containing multi-heterocyclic compound provided by the invention takes a multi-heterocyclic structure compound as a matrix, and an electron-donating group is introduced into the matrix structure, so that a novel OLED material which has a high triplet state energy level, a good carrier mobility, a high thermal stability and a high film forming stability and can be matched with an adjacent layer energy level is obtained. The material can be applied to the field of organic electroluminescence, can be used as a green light main body material, and can effectively improve the photoelectric property of a device.
Detailed Description
The following examples are intended to illustrate the present invention, but are not intended to limit the scope of the present invention, and other equivalent changes or modifications made without departing from the spirit of the present invention are intended to be included within the scope of the appended claims.
According to the preparation method provided by the present invention, a person skilled in the art can use known common means to implement, such as further selecting a suitable catalyst and a suitable solvent, and determining a suitable reaction temperature, a suitable reaction time, a suitable material ratio, and the like, which are not particularly limited in the present invention. If not specifically stated, the starting materials for the preparation of solvents, catalysts, bases, etc. may be obtained by published commercial routes or by methods known in the art.
EXAMPLE 1 Synthesis of intermediate M1
Figure BDA0002611575710000151
The synthetic route is as follows:
Figure BDA0002611575710000152
the method comprises the following specific steps:
(1) Adding 4-chloro-1-fluoro-2-nitrobenzene (17.5g, 0.1mol) and 2-bromo-4-chloroaniline (30.8g, 0.15mol) into a 2L three-neck flask with mechanical stirring, carrying out argon protection, heating to 180 ℃, carrying out heat preservation reaction for more than 30 hours, wherein the color of a reaction liquid gradually becomes red in the reaction process, and finally gradually becomes deep red;
(2) After the reaction is finished, separating an organic phase, extracting, drying, carrying out column chromatography, and spin-drying a solvent to obtain 30g of orange-red solid M-01 with the yield of 83%;
(3) In a 2L three-necked flask equipped with a mechanical stirrer, M-01 (36.0 g,0.1 mol), sodium sulfide nonahydrate (96g, 0.4 mol), ethanol (200 mL), water (100 mL), and nitrogen were added, and the mixture was heated to reflux and refluxed for 3 hours to complete the reaction. Separating an organic phase, extracting, drying, carrying out column chromatography, and spin-drying the solvent to obtain 26.5g of white solid M-02 with the yield of 80%;
(4) In a 1L three-necked flask equipped with a mechanical stirrer, M-02 (33.0 g, 0.1mol) and 300mL of acetone were added to be completely dissolved, a solution of KOH (11.2 g,0.2 mol) dissolved in water (50 mL) was added, then 2-bromo-4-chlorobenzoyl chloride (25.2 g, 0.1mol) was slowly dropped into the flask, solids were gradually precipitated from the flask, and after the dropping, the reaction was carried out at room temperature for 2 hours, and the reaction was completed. Adjusting to neutrality, separating an organic phase, extracting, drying, performing column chromatography, and spin-drying the solvent to obtain 43.8g of white solid M-03 with a yield of 79%;
(5) Adding M-03 (54.8g, 0.1mol) into a 1L three-necked bottle, adding 200mL of diethylene glycol dimethyl ether under the protection of nitrogen, gradually heating to reflux, gradually dissolving a solid, magnetically stirring, keeping the temperature and reacting for 3 hours, and finishing the reaction. Separating an organic phase, extracting, drying, carrying out column chromatography, and spin-drying the solvent to obtain 40.0g of light red solid M-04 with the yield of 76%;
(6) Under the protection of nitrogen, M-04 (53.0 g, 0.1mol) and 800mL of THF were added into a 2L three-necked flask, the mixture was cooled to-78 ℃, n-butyllithium (100mL, 0.25mol) was slowly added dropwise under stirring for about 30mins, 5mL of THF was used to flush the dropping funnel, and the mixture was allowed to warm for 1.5 hours to obtain M-05 reaction solution. Heating the reaction system to-30 ℃, slowly passing dry oxygen through the reaction liquid, keeping ventilation for 5 hours, keeping the temperature for 1 hour, slowly heating to room temperature, adding saturated ammonium chloride aqueous solution to quench the reaction, adjusting the system to be neutral, adding ferrous chloride aqueous solution, stirring and reacting for 4 hours at room temperature, wherein the solution turns into yellow brown, and the starch-potassium iodide test paper does not change color. The organic phase was separated, extracted, dried and the solvent was spin dried to give a tan solid.
Dissolving the solid in 300ml of diethylene glycol dimethyl ether in a 1L reaction bottle, adding 5g of p-toluenesulfonic acid monohydrate (0.026 mol), heating to 150 ℃, stirring for reaction for 5 hours until TLC detection raw materials disappear, cooling a reaction system, adding 200ml of saturated saline solution and 200ml of dichloromethane for extraction for three times, combining organic phases, drying by anhydrous magnesium sulfate, spin-drying a solvent, and performing column chromatography to obtain 20g of a white solid intermediate M1 with the yield of 51%.
Product MS (m/e): 386; elemental analysis (C) 19 H 9 Cl 3 N 2 O): theoretical value C:58.87%, H:2.34%, N:7.23 percent; measured value C:58.67%, H:2.54%, N:7.43 percent.
Example 2: synthesis of intermediate M2
Figure BDA0002611575710000161
By using
Figure BDA0002611575710000162
Respectively replace
Figure BDA0002611575710000163
The intermediate M2 is obtained by selecting a proper material ratio and the other raw materials and steps are the same as those of the example 1.
Product MS (m/e): 352; elemental analysis (C) 19 H 10 Cl 2 N 2 O): theoretical value C:64.61%, H:2.85%, N:7.93 percent; found value C:64.41%, H:2.95%, N:7.83 percent.
Example 3: synthesis of intermediate M3
Figure BDA0002611575710000164
By using
Figure BDA0002611575710000165
Substitute for
Figure BDA0002611575710000166
The intermediate M3 was obtained by selecting the appropriate material ratio and the same procedure as in example 1 for the other raw materials.
Product MS (m/e): 352; elemental analysis (C) 19 H 10 Cl 2 N 2 O): theoretical value C:64.61%, H:2.85%, N:7.93 percent; found value C:64.63%, H:2.79%, N:7.84 percent.
Example 4: synthesis of intermediate M4
Figure BDA0002611575710000171
By using
Figure BDA0002611575710000172
Substitute for
Figure BDA0002611575710000173
The intermediate M4 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product ofMS (m/e): 352; elemental analysis (C) 19 H 10 Cl 2 N 2 O): theoretical value C:64.61%, H:2.85%, N:7.93 percent; found value C:64.49%, H:2.90%, N:7.76 percent.
Example 5: synthesis of intermediate M5
Figure BDA0002611575710000174
By using
Figure BDA0002611575710000175
Respectively replace
Figure BDA0002611575710000176
The intermediate M5 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product MS (m/e): 318; elemental analysis (C) 19 H 11 ClN 2 O): theoretical value C:71.59%, H:3.48%, N:8.79 percent; found value C:71.48%, H:3.39%, N:8.82 percent.
Example 6: synthesis of intermediate M6
Figure BDA0002611575710000177
By using
Figure BDA0002611575710000178
Respectively replace
Figure BDA0002611575710000179
The intermediate M6 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product MS (m/e): 318; elemental analysis (C) 19 H 11 ClN 2 O): theoretical value C:71.59%, H:3.48%, N:8.79 percent; found value C:71.63%, H:3.27%, N:8.61 percent.
Example 7: synthesis of intermediate M7
Figure BDA0002611575710000181
By using
Figure BDA0002611575710000182
Respectively replace
Figure BDA0002611575710000183
The intermediate M7 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product MS (m/e): 318; elemental analysis (C) 19 H 11 ClN 2 O): theoretical value C:71.59%, H:3.48%, N:8.79 percent; found value C:71.45%, H:3.34%, N:8.89 percent.
Example 8: synthesis of intermediate M8
Figure BDA0002611575710000184
By using
Figure BDA0002611575710000185
Instead of the former
Figure BDA0002611575710000186
The intermediate M8 was obtained by selecting the appropriate material ratio and the same procedure as in example 1 for the other raw materials.
Product MS (m/e): 352; elemental analysis (C) 19 H 10 Cl 2 N 2 O): theoretical value C:64.61%, H:2.85%, N:7.93 percent; found value C:64.49%, H:2.65%, N:7.78 percent.
Example 9: synthesis of intermediate M9
Figure BDA0002611575710000187
(1) Synthesis of intermediate M9-04:
by using
Figure BDA0002611575710000188
Respectively replace
Figure BDA0002611575710000189
Selecting a proper material ratio, and obtaining M9-04 by using other raw materials and steps which are the same as those in the example 1;
(2) Synthesis of intermediate M9: in N 2 Under protection, M9-04 (58.8g, 0.1mol) and 500ml of anhydrous THF are added into a 2L three-necked bottle, the reaction system is cooled to-78 ℃ by a liquid nitrogen ethanol bath under stirring, 70ml of a 1.6M hexane solution (0.11 mol) of n-butyllithium is slowly added at the temperature, after complete dropwise addition, the temperature is kept for 15 minutes at the temperature, then the reaction system is heated to-30 ℃, dry oxygen is slowly introduced into the reaction liquid, bubbling reaction is carried out for 5 hours at the temperature, the temperature is kept for 1 hour at the temperature, then the temperature is slowly raised to room temperature, a saturated ammonium chloride water solution is added to quench the reaction, then the system is adjusted to be neutral, a ferrous chloride water solution is added, the reaction is stirred at the room temperature for 4 hours, the solution becomes yellow brown, and the color is not changed by a starch-potassium iodide test paper. The organic phase was separated, extracted, dried and the solvent was spin dried to give a tan solid.
Into a 1L three-necked flask, the above tan solid, 300ml of dioxane, cuI (5.7 g, 0.03mol), N, N-dimethyl-glycine (10.3 g,0.1 mol), cesium carbonate (64g, 0.2 mol) were added, and the reaction mixture was stirred at 60 ℃ for 3 hours, and the progress of the reaction was monitored by TLC to completion. Cooling to room temperature, slowly adding saturated ammonium chloride solution, adding 250ml of ethyl acetate, separating the organic phase, extracting the aqueous phase with ethyl acetate for 3 times, combining the organic phases, drying with anhydrous magnesium sulfate, spin-drying the solvent, and separating by column chromatography to obtain 17.1g of the intermediate M9 altogether, and obtaining a white solid with a yield of about 41% in the two steps.
Product MS (m/e): 396; elemental analysis (C) 19 H 10 BrClN 2 O): theoretical value C:57.39%, H:2.53%, N: 7.04 percent; found value C:57.49%, H:2.38%, N:6.89 percent.
Example 10: synthesis of intermediate M10
Figure BDA0002611575710000191
By using
Figure BDA0002611575710000192
Respectively replace
Figure BDA0002611575710000193
The intermediate M10 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 9.
Product MS (m/e): 396; elemental analysis (C) 19 H 10 BrClN 2 O): theoretical value C:57.39%, H:2.53%, N: 7.04 percent; found value C:57.51%, H:2.45%, N:6.97 percent.
Example 11
Figure BDA0002611575710000194
Synthesis of (Compound I-16)
The synthetic route is as follows:
Figure BDA0002611575710000201
the method comprises the following specific steps:
synthesis of Compound I-16
A 1L three-necked flask is stirred by magnetic force, M1 (38.8g, 0.1mol), (9-phenyl-9H-carbazole-3-yl) boric acid (86.1g, 0.3mol), cesium carbonate (117g, 0.36mol) and dioxane 400ml are sequentially added after nitrogen replacement, and stirring is started; after the nitrogen substitution again, (2.2 g, 11mmol) tri-tert-butylphosphine and (4.1g, 4.5mmol) tris (dibenzylideneacetone) dipalladium were added. After the addition, heating and raising the temperature, controlling the temperature to be 80-90 ℃ for reaction for 4 hours, and cooling after the reaction is finished. Adjusting to neutrality, separating an organic phase, extracting, drying, performing column chromatography, and spin-drying the solvent to obtain 76.6g of pale yellow solid with the yield of about 76%.
Product MS (m/e):1007; elemental analysis (C) 73 H 45 N 5 O): theoretical value C:86.97%, H:4.50%, N:6.95%,; found value C:86.77%, H:4.72%, N:6.65 percent.
Example 12
Figure BDA0002611575710000202
Synthesis of (Compound I-26)
The synthetic route is as follows:
Figure BDA0002611575710000203
synthesis of Compound I-26
M2 is used for replacing M1, and (4- (9H-carbazole-9-yl) phenyl) boric acid is used for replacing (9-phenyl-9H-carbazole-3-yl) boric acid, the proper material ratio is selected, other raw materials and steps are the same as those of example 11, 64.4g of light yellow solid is obtained, and the yield is about 84%.
Product MS (m/e): 766; elemental analysis (C) 55 H 34 N 4 O): theoretical value C:86.14%, H:4.47%, N:7.31 percent; found value C:86.34%, H:4.27%, N:7.51 percent.
Example 13
Figure BDA0002611575710000211
Synthesis of (Compound I-45)
The synthetic route is as follows:
Figure BDA0002611575710000212
the method comprises the following specific steps:
synthesis of Compound I-45
M3 was used in place of M1, and (9- (naphthalene-2-yl) -9H-carbazol-3-yl) boronic acid was used in place of (9-phenyl-9H-carbazol-3-yl) boronic acid, and the other raw materials and procedures were the same as in example 11, selecting an appropriate material ratio, to give 72.8g of a pale yellow solid with a yield of about 84%.
Product MS (m/e): 866; elemental analysis (C) 63 H 38 N 4 O): theoretical value C:87.27%, H:4.42%, N:6.46 percent; found value C:87.47%, H:4.30%, N:6.59 percent.
Example 14
Figure BDA0002611575710000213
Synthesis of (Compound I-62)
The synthetic route is as follows:
Figure BDA0002611575710000214
synthesis of Compound I-62
M4 was used in place of M1, and (5-phenyl-5H-benzo [ b ] carbazol-2-yl) boronic acid was used in place of (9-phenyl-9H-carbazol-3-yl) boronic acid, and the other raw materials and procedures were the same as in example 11, selecting an appropriate material ratio, to obtain 74.6g of a pale yellow solid with a yield of about 86%.
Product MS (m/e): 866; elemental analysis (C) 63 H 38 N 4 O): theoretical value C:87.27%, H:4.42%, N:6.46 percent; found value C:87.47%, H:4.55%, N:6.59 percent.
Example 15
Figure BDA0002611575710000221
Synthesis of (Compound I-81)
The synthetic route is as follows:
Figure BDA0002611575710000222
the method comprises the following specific steps:
synthesis of Compound I-81
Using M5 instead of M1, (4- (7H-dibenzo [ c, g ] carbazol-7-yl) phenyl) boronic acid instead of (9-phenyl-9H-carbazol-3-yl) boronic acid, the appropriate material ratios were chosen and the other raw materials and procedures were the same as in example 11 to give 51.3g of a pale yellow solid with a yield of about 82%.
Product MS (m/e): 625, a first step of; elemental analysis (C) 45 H 27 N 3 O): theoretical value C:86.38%, H:4.35%, N:6.72 percent; found value C:86.58%, H:4.55%, N:6.40 percent.
Example 16
Figure BDA0002611575710000223
Synthesis of (Compound I-101)
The synthetic route is as follows:
Figure BDA0002611575710000224
the method comprises the following specific steps:
synthesis of Compound I-101
Substituting M6 for M1 and (4- (10-phenylindole [3,2-b ] indol-5 (10H) -yl) phenyl) boronic acid for (9-phenyl-9H-carbazol-3-yl) boronic acid with the appropriate material ratios and the other starting materials and procedures were the same as in example 11, yielding 53.2g of a pale yellow solid in about 83% yield.
Product MS (m/e): 640; elemental analysis (C) 45 H 28 N 4 O): theoretical value C:84.35%, H:4.40%, N:8.74 percent; found value C:84.55%, H:4.54%, N:8.88 percent.
Example 17
Figure BDA0002611575710000231
Synthesis of (Compound I-121)
The synthetic route is as follows:
Figure BDA0002611575710000232
the method comprises the following specific steps:
synthesis of Compound I-121
Using M7 in place of M1, (4- (11H-benzo [4,5] thieno [3,2-b ] carbazol-11-yl) phenyl) boronic acid in place of (9-phenyl-9H-carbazol-3-yl) boronic acid, the appropriate material ratios were chosen and the other raw materials and procedures were the same as in example 11 to give 51.2g of a pale yellow solid with a yield of about 81%.
Product MS (m/e): 631; elemental analysis (C) 43 H 25 N 3 OS): theoretical value C:81.75%, H:3.99%, N:6.65 percent; found value C:81.88%, H:3.79%, N:6.75 percent.
Example 18
Figure BDA0002611575710000233
Synthesis of (Compound I-139)
The synthetic route is as follows:
Figure BDA0002611575710000234
the method comprises the following specific steps:
synthesis of Compound I-139
M8 was used in place of M1, and (3-phenylbenzo [ b ] thiophen-2-yl) boronic acid was used in place of (9-phenyl-9H-carbazol-3-yl) boronic acid in the same manner as in example 11 except for the use of M8 and the selection of an appropriate material ratio, to obtain 56.1g of a pale yellow solid with a yield of about 80%.
Product MS (m/e): 700 of the base material; elemental analysis (C) 47 H 28 N 2 OS 2 ): theoretical value C:80.54%, H:4.03%, N:4.00 percent; found value C:80.74%, H:4.23%, N:4.18 percent.
Example 19
Figure BDA0002611575710000241
Synthesis of (Compound I-185)
The synthetic route is as follows:
Figure BDA0002611575710000242
the method comprises the following specific steps:
synthesis of Compound I-185
Into a 1L three-necked flask, M9 (39.8g, 0.1mol), (9- (naphthalen-2-yl) -9H-carbazol-3-yl) boronic acid (33.7g, 0.1mol, purity 99%), sodium carbonate (21.2g, 0.2mol), toluene (150 mL), ethanol (150 mL), and water (150 mL) were charged, and Pd (PPh) was added after the reaction system was purged with nitrogen 3 ) 4 (11.5g, 0.01mol). The reaction was heated under reflux (temperature in the system: about 78 ℃ C.) for 3 hours to stop the reaction. Distilling off the solvent, extracting with dichloromethane, drying with anhydrous magnesium sulfate, filtering, performing petroleum ether/ethyl acetate (2:1) column chromatography, spin-drying the solvent, pulping the ethyl acetate, and filtering to obtain 50.6g of pale yellow solid I-185-1 with the yield of about 83%;
A1L three-necked flask was stirred by magnetic stirring, and after nitrogen substitution, I-185-1 (61.0g, 0.1mol), (9-phenyl-9H-carbazol-3-yl) boric acid (28.7g, 0.1mol), cesium carbonate (39g, 0.12mol), and 400ml dioxane were added in this order, followed by stirring. After the nitrogen substitution again, (0.8g, 4mmol) tri-tert-butylphosphine and (1.4g, 1.5mmol) tris (dibenzylideneacetone) dipalladium were added. After the addition, heating and raising the temperature, controlling the temperature to be 80-90 ℃ for reaction for 4 hours, and cooling after the reaction is finished. Adjusting to neutrality, separating organic phase, extracting, drying, column chromatography, and spin-drying solvent to obtain 62.0g pale yellow solid I-185 with yield of about 76%.
Product MS (m/e): 816; elemental analysis (C) 59 H 36 N 4 O): theoretical value C:86.74%, H:4.44%, N:6.86 percent; found value C:86.94%, H:4.24%, N:6.56 percent.
Example 20
Figure BDA0002611575710000243
Synthesis of (Compound I-189)
The synthetic route is as follows:
Figure BDA0002611575710000244
substituting M10 for M9, (4- (10-phenylindole [3,2-b ] indol-5 (10H) -yl) phenyl) boronic acid and dibenzo [ b, d ] furan-2-yl boronic acid for (9- (naphthalen-2-yl) -9H-carbazol-3-yl) boronic acid and (9-phenyl-9H-carbazol-3-yl) boronic acid, respectively, selecting appropriate material ratios and the other raw materials and procedures were the same as in example 19 to give 60.5g of I-189 as a pale yellow solid in about 75% yield.
Product MS (m/e): 806; elemental analysis (C) 57 H 34 N 4 O 2 ): theoretical value C:84.84%, H:4.25%, N:6.94 percent; found value C:84.54%, H:4.45%, N:6.74 percent
According to the technical schemes of the examples 1 to 20, other compounds of I-1 to I-190 can be synthesized only by simply replacing corresponding raw materials and not changing any substantial operation.
Device examples the compounds of the invention were used as green host materials
The embodiment provides a group of OLED green light devices, and the structure of the device is as follows:
ITO/HATCN (1 nm)/HT 01 (40 nm)/NPB (20 nm)/EML (30 nm) (containing I-16)/Bphen (40 nm)/LiF (1 nm)/Al.
The molecular structure of each functional layer material is as follows:
Figure BDA0002611575710000251
the preparation method comprises the following steps:
(1) Carrying out ultrasonic treatment on the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, washing the glass plate in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent (the volume ratio is 1: 1), baking the glass plate in a clean environment until the water is completely removed, cleaning the glass plate by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
(2) Placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10 -5 ～9×10 -3 Pa, performing vacuum evaporation on the anode layer film to form HATCN as a first hole injection layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 1nm; then, a second hole injection layer HT01 is evaporated at a rate of 0.1nm/s,the thickness is 40nm; then evaporating a hole transport layer material NPB at the evaporation rate of 0.1nm/s and the evaporation film thickness of 20nm;
(3) EML is vacuum evaporated on the hole transport layer to serve as a light emitting layer of the device, the EML comprises the main material I-16 and the dye material, the evaporation rate of the main material is adjusted to be 0.1nm/s by a multi-source co-evaporation method, and the dye material Ir (piq) 2 The acac concentration is 5%, the total film thickness is 30nm, and CBP is used as a contrast material of a main body material;
(4) Taking Bphen as an electron transport layer material of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 40nm;
(5) LiF with the thickness of 1nm is sequentially subjected to vacuum evaporation on the electron transport layer to serve as an electron injection layer, and an Al layer with the thickness of 150nm serves as a cathode of the device.
And (3) respectively obtaining the OLED-2-OLED-10 provided by the invention by respectively replacing I-16 in the step (3) with I-26, I-45, I-62, I-81, I-101, I-121, I-139, I-185 and I-189 according to the same steps.
Following the same procedure as above, only replacing I-16 in step (3) with CBP (comparative compound), comparative example OLED-11 provided by the present invention was obtained. The structure of the CBP is specifically as follows:
Figure BDA0002611575710000261
the performance of the obtained devices OLED-1 to OLED-11 is detected, and the detection results are shown in Table 1.
Table 1: performance test results of OLED devices
Figure BDA0002611575710000262
From the above, the devices OLED-1 to OLED-10 prepared by using the organic material shown in formula I provided by the invention have higher current efficiency, and under the condition of the same brightness, the working voltage is obviously lower than that of the device OLED-11 using CBP as the main material, so that the organic material is a green light main material with good performance.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.

Claims (9)

1. An oxygen-containing polyheterocyclic compound, which is characterized by having a structure shown in a general formula (I):
Figure FDA0003826995250000011
in the general formula (I):
R 1 ～R 12 any one of the groups is a substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring; or, said R 1 ～R 12 Any two groups are substituted or unsubstituted aromatic groups containing five-membered heterocyclic rings, and the two groups can be the same or different; or, said R 1 ～R 12 Any three groups are substituted or unsubstituted aromatic groups containing five-membered heterocyclic rings, and the three groups can be the same, any two of the three groups can be the same, different from the rest one of the three groups, and can also be different from each other; the aromatic group containing the five-membered heterocycle is connected with a mother nucleus shown in a general formula (I) through a C atom;
the R is 1 ～R 12 Wherein the rest of the aromatic groups are hydrogen atoms except for substituted or unsubstituted aromatic groups containing five-membered heterocyclic rings;
the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from:
Figure FDA0003826995250000012
Figure FDA0003826995250000021
Figure FDA0003826995250000031
in each of the above-mentioned substituent groups, "- - -" represents a substitution position.
2. The compound of claim 1, wherein the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from the group consisting of:
Figure FDA0003826995250000032
Figure FDA0003826995250000041
3. the compound of claim 1, wherein the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from the group consisting of:
Figure FDA0003826995250000042
4. the compound of claim 1, selected from the structures represented by formulas I-1 to I-190 below:
Figure FDA0003826995250000043
Figure FDA0003826995250000051
Figure FDA0003826995250000061
Figure FDA0003826995250000071
Figure FDA0003826995250000081
Figure FDA0003826995250000091
Figure FDA0003826995250000101
Figure FDA0003826995250000111
Figure FDA0003826995250000121
5. use of the oxygen-containing heterocyclic compound of any one of claims 1 to 4 for the preparation of an organic electroluminescent device.
6. An organic electroluminescent device comprising an electroluminescent layer, wherein the oxygen-containing heterocyclic compound according to any one of claims 1 to 4 is contained in a green host material of the electroluminescent layer.
7. The organic electroluminescent device according to claim 6, wherein the organic electroluminescent device comprises, from bottom to top, a transparent substrate, an anode layer, a hole transport layer, an electroluminescent layer, an electron transport layer, an electron injection layer, and a cathode layer; wherein the green host material of the electroluminescent layer contains the oxygen-containing heterocyclic compound according to any one of claims 1 to 4.
8. A display apparatus comprising the organic electroluminescent device according to claim 6 or 7.
9. An illumination apparatus comprising the organic electroluminescent device according to claim 6 or 7.
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CN110483529A (en) * 2019-08-09 2019-11-22 宁波卢米蓝新材料有限公司 A kind of fused heterocyclic compound and its application
CN111253374A (en) * 2020-03-31 2020-06-09 烟台显华化工科技有限公司 Naphtho five-membered ring benzo fused heterocycle organic compound and application thereof

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CN110483529A (en) * 2019-08-09 2019-11-22 宁波卢米蓝新材料有限公司 A kind of fused heterocyclic compound and its application
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